(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester

Base Information

• Chemical Name: (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester
• CAS No.: 503446-40-0
• Molecular Formula: C₃₇H₅₇BrO₆
• Molecular Weight: 677.76
• Mol file: 503446-40-0.mol

Synonyms:(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester

Chemical Property of (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester

There total 1 articles about (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(4R,5R,8S,12R)-4,7-Bis-benzyloxy-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester → (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester (503446-40-0)

Guidance literature:

(4R,5R,8S,12R)-4,7-Bis-benzyloxy-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester; With chloro-trimethyl-silane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

With N-Bromosuccinimide; at 20 ℃;

DOI:10.1016/S0040-4039(02)02603-5

Reference yield: 90.0%

(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester (503446-40-0) → (4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester (503446-41-1)

Guidance literature:

With Amberlyst 15; In water; acetone;

DOI:10.1016/S0040-4039(02)02603-5

Reference yield:

(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-15,15-dimethoxy-8,12-dimethyl-pentadecanoic acid methyl ester (503446-40-0) → (4R,5R,7S,8S,12R)-4,7-Bis-benzyloxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester (503546-23-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / Amberlyst 15 / acetone; H₂O

2: SmI₂ / tetrahydrofuran / 0 °C

3: Et₃N / CH₂Cl₂ / 20 °C

4: DBU / toluene / 10 h / Heating

5: 70 percent / mCPBA / CH₂Cl₂ / 20 °C

With Amberlyst 15; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; samarium diiodide; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 2: intramolecular Reformatsky reaction;

DOI:10.1016/S0040-4039(02)02603-5

Downstream raw materials:

(4R,5R,8S,12R)-4,7-Bis-benzyloxy-2-bromo-5-isopropyl-8,12-dimethyl-15-oxo-pentadecanoic acid methyl ester

(4R,5R,7S,8S,12R)-4,7-Bis-benzyloxy-5-isopropyl-8,12-dimethyl-15-oxa-bicyclo[12.1.0]pentadecane-2-carboxylic acid methyl ester

(Z)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-12-isopropyl-5,9-dimethyl-cyclotetradec-2-enecarboxylic acid methyl ester

(E)-(5R,9S,10S,12R,13R)-10,13-Bis-benzyloxy-12-isopropyl-5,9-dimethyl-cyclotetradec-1-enecarboxylic acid methyl ester